Ethanol → {3-Methoxy-4-[(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)methoxy]phenyl}methanol

HRID 2221558Notes

Reaction equation

HRID 2221558 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[S:16][C:17]=1[CH3:18])[CH:6]=[O:7].C(O)C.[BH4-].[Na+].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[S:16][C:17]=1[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 866057113-Methoxy-4-[(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)methoxy]benzaldehyde

Product 1

HCID 69216168{3-Methoxy-4-[(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)methoxy]phenyl}methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxy-4-[(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)methoxy]benzaldehyde (0.50 g) in tetrahydrofuran (5 mL)-ethanol (5 mL) was gradually added sodium borohydride (0.05 g) at room temperature. After stirring for 1 hr, water was added to the reaction mixture and the precipitated crystals were collected by filtration to give {3-methoxy-4-[(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)methoxy]phenyl}methanol as colorless crystals (0.44 g, yield 90%). melting point: 92-93° C.

Workup

  1. customat room temperature
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-bd102395d3ad4021817ccb6afa1b01e0
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…